The Super Bowl Bet Pt. 02

Part 2: It's going to be a long week

I arrived at Allison's house on Friday night as required. Both Ann and Ashley were there as well. Allison began by asking for my car keys, wallet and cell phone. "You won't be needing these this week, and as long as I have them, you will think twice about leaving." She took the items to her car and locked them inside so I could not get to them. When she returned she let me know what to expect during the coming week.

"This week you will be our boy toy. You will remain naked and serve any woman who enters this house. Failure to perform an assigned task properly will result in punishment. Failure to address any woman with respect will result in punishment. Failure to achieve an erection on demand will result in punishment. Do you understand your responsibilities?"

"Yes Allison."

"That's Miss Allison. You will address all women as Ma'am or by their name preceded by Miss or Mistress." You have earned your first punishment for disrespect, Strip and bend over."

Miss Allison proceeded to administer 10 strokes with a leather paddle to my naked bottom. Following the punishment I was order to crawl to each of the women present, kiss her feet and ass, and beg to be allowed to serve her during the week. I went from Miss Allison to Miss Ashley and finally Miss Ann; begging each of them to allow me to serve them. When I had completed my task I heard laughter coming from behind me. I turned to see Sarah, my step sister and Samantha, her sister. Both were looking at me with amusement.

Let me tell you a little about my step sisters. Sarah is a year older than me. She has always been a little plump, and I would always tease her about it when growing up. I would play tricks on her and basically try to make her life miserable. Today, she stands about 5'10" and weighs about 160 lbs. She's what one would call a "full figured" lady, although I would not call her fat. She has brown hair which she keeps cut short. Samantha is 6 years older than me, making her 41. She has been married once which ended in divorce. As she has gotten older she has put on a few extra pounds and could be considered a BBW. We never really saw much of each other growing up as she was away at college when her mom came to live with us, but I remember her as having a bossy attitude which is probably why her marriage failed. Anyway, I quickly got the impression that their being here would not be good for me.

Sarah was the first to speak. "Well Dean, I guess you thought I was doing you a favor in setting you up with Allison. In reality, I was paying you back for all the heartache you caused me growing up. You see Allison and I have been lovers for 2 years. No, we're not lesbians, we are both bisexual. The thing is, when we have sex with men, we always take the dominant role. Allison is ready to settle down. She wants to experience a Female Led Marriage and has been looking for the right male to dominate. I told her about you, your history with women, and your treatment of me during childhood. She thought you would be the perfect challenge to convert into a submissive husband. Looks like your training will start this week, and guess what? Sam and I will be here to help her out. Won't that be fun?"

Samantha walked up to me a put her boot in my face. "Go ahead and kiss it, then my ass. Beg me to allow you to serve me this week. When you finish, go do the same for Sarah."

I couldn't believe what I was hearing. I had been set up by my own step sister and now had to serve these women for a week, maybe more. Friday night was a blur, no matter what I did, I couldn't avoid being punished over and over. They would create new rules throughout the night just to give themselves an opportunity to punish me for breaking them. They would humiliate me as often as possible, and constantly kept my cock erect through teasing. If I dripped pre-come or worse yet, ejaculated without permission I was forced to eat my semen and then was spanked, paddled or whipped for my transgression. I was required to orally service them for hours at a time. I ate more pussy, kissed more ass, and worshipped more feet than I had done in my entire life. Around 2 AM they finally got too tired to continue. Miss Allison brought out a bag of ice and wrapped it around my cock causing it to shrink. Once soft she placed a chastity device on me and locked it with a key.

"You will not be getting any relief tonight. Tomorrow your real training starts. Go up to the spare bedroom and get some rest. You will sleep on the floor next to Samantha's bed. Wake us at 8 am."

I tried to sleep that night, but the pain in my cock from the inferno chastity device as well as the pain to my ass and back from the countless paddling and whippings made sleep difficult. I must have dozed some because I was awakened at 7 o'clock by Samantha, who then rolled over and went back to sleep. I cleaned myself up as best I could, and at 8 am went into Miss Allison's room to wake her.

"Get down and give my pussy a nice wakeup call" she demanded. "When finished, wake each of the other ladies in a similar fashion starting with your step sister Sarah. Then, go and make us breakfast. I will be down shortly to supervise."

Waking each of the ladies took longer than expected, and several required a long session of pussy worship. Miss Allison was waiting for me when I arrived in the kitchen.

"You have earned another punishment for keeping me waiting" she said. "I will put it on my to-do list for today since I am hungry. Fix my breakfast, and make it good or risk additional punishment."

As I started preparing breakfast she sat at the table writing down a list of chores and duties I was to perform that day. The other ladies soon accompanied her at the table and made further suggestions to add to her list. When breakfast was ready I served it in the dining room. All of the ladies ate and complemented my on my cooking. "At least there is something you can do right" one of them commented. "At least we will eat well this week."

I looked at the list that they had compiled and I realized that there was no way I would be able to complete it. Miss Allison had to go to work and Miss Ashley was heading out to the gym and to run some errands. This left me with Miss Ann and my two step sisters. I wasn't looking forward to the rest of the day. I began with cleaning up the kitchen from breakfast. I was able to eat what the ladies had left, but I was still hungry when I finished. After finishing in the kitchen I was off to straighten each of the bedrooms the ladies had slept in last night. It was obvious that Sarah and Allison had slept together in her king sized bed. The second bedroom was Ann's and it appeared she had slept alone. Ashley slept in a third bedroom and Samantha had the guest bedroom with me on the floor. After straightening each of the rooms, changing their bed linens and tidying up their bathrooms, I went back downstairs to see what was next on the list.

There was laundry to do, floors to scrub, furniture to dust and vacuuming to do. The ladies supervised with paddles and made comments on how things should be done, deficiencies in performance, and on two occasions how I disrespected them by getting an erection without permission. All in all I earned 10 punishments in addition to the one Miss Allison had bestowed upon me that morning. I was told I would receive them tonight after dinner.

Dinner was served at 6 pm. I prepared chicken parmesan and salad and made sure I prepared enough so that I would have plenty of left overs since I was famished from serving Ann and my step sisters all day. Once dinner was over and the kitchen straightened, I was summoned to the dining room where the ladies were enjoying the last of a bottle of wine.

Allison said. "I understand you were less than stellar in your performance today, and were disrespectful as well by obtaining an erection without permission. You will now be punished for your actions. In fact, there is a punishment waiting for you for keeping me waiting this morning isn't there?"

"Yes, Miss Allison" I replied

"Very well. We will proceed to the basement. You have not seen this part of the house, and it will be a little frightening to you when you first see it. However, you will become quite familiar with it before you are allowed to leave."

As we proceeded down the stairs into the basement, me crawling behind Miss Allison and the other ladies following with crop in hand, I was becoming more and more nervous of what was about to take place. Miss Ann occasionally swatted my butt when I did not move fast enough and Miss Allison would pull on the chain attached to the collar around my neck. Miss Allison opened the basement door and what I saw did indeed frighten me. Before me was what could only be described as a fully equipped dungeon. There was a rack full of paddles and whips, a cross, a device that looked like a stocks, a pillory and several pieces of furniture I didn't understand at the time. I was sure I would be acquainted with each before the week was through. Various rope and chains hung from the walls. There was even a winch attached to the ceiling.

Miss Allison dragged me over to the rack and attached me spread eagle to it with my butt fully exposed. "Punishments are designed to modify undesirable behaviors and mold the individual into performing in an acceptable manner. In order for a punishment to be effective, the individual must learn there will be consequences for their undesirable actions. You will learn this tonight. You have earned 11 separate punishments which is a lot, even for an experienced slave. You had better learn how to minimize these punishments in the future or its going to be a painful three weeks for you."

As I looked over at the other ladies staring at me I saw each had a smile on her face. It was evident that they enjoyed administering pain, and that I was probably not the first person to endure their wrath. The first punishment was a paddling from each of the ladies with a sorority paddle that Ann had kept from college. It was a typical wooden paddle with holes drilled in the business end and the Greek letters sigma-sigma-sigma engraved into it.

Ann took the paddle and said. "This is for failing to properly make my bed this morning. You will receive 20 swats from each of us. If you should get an erection at any time during the paddling, I will whip it off of you and start over. Is that clear?"

"Yes Ma'am I replied," and from the very first stoke I was sure that I didn't have to worry about an erection. Each swing of the paddle ended with a painful "thud" on my ass and by the time Miss Ann was through my ass was as red as the red thong panties I was made to wear. Samantha was next, and if anything, her swats were more vicious than Ann's. Each woman proceeded to bust my butt. Ashley, the free spirit was last to go. I thought that maybe she would have some pity on me, given her happy-go-lucky attitude, but unfortunately for me, she proved to me as stern a disciplinarian as each of the other ladies, and the leverage she produced using her long arms to swing the paddle reminded me of a professional tennis player making a forehand return. By the time they were done I was crying like never before and begging for them to stop.

I was given a few minutes to recover while they went to get another bottle of wine. When they returned they released me from the cross only to reattach me facing outward. This time it was Sarah who spoke. "Your second offense was to disrespect me by getting an erection in front of me while washing my panties this morning. I even caught you sniffing them once. You will learn that you are to achieve erection only when ordered to. Failure to do so, or obtaining one without permission will result in punishment. You should be doubly ashamed of getting an erection in front of your step sister. For this punishment, each lady will stroke your cock until hard. She will not stop until you are ready to explode. If you cum without permission, the paddling you just received will be repeated. The lady will then take this penis whip and whip your cock until you are soft again. Off course, she is free to stroke you some more to try to prolong the whipping.

I looked at the penis whip and saw a whip with a short braided handle which ended in a number of leather strips. It looked like a miniature cat-o-nine tails I had seen pictures of. Sarah began stroking me and after a while my cock responded to her touch. She continued long after I had become erect and soon I was begging her to stop, fearful of cumming. Finally, she picked up the whip and began. After about 20 strokes she was satisfied with the results. Allison went next. My cock was still hurting from the previous whipping so it was difficult for her to get me hard. She stopped her stroking, bent down and took my cock into her mouth. It was like nothing I had ever felt before. She was an expert in teasing my cock and finally it was as hard as ever. She picked up the whip and smiled.

"Sarah gave you 20 strokes before she was satisfied. You had better allow me at least that number of strokes or I will be extremely unhappy, and remember I get to select your next punishment." Thirty strokes later she was satisfied I had been sufficiently chastised. "Next" she said and Ann stepped forward. By the time each of them had a turn my penis was raw and my balls blue.

The rest of the evening followed suit. I was beaten, teased, restrained and humiliated by each of my five mistresses. I licked pussy and ass, sucked on toes and feet, and massaged their bodies until each was satisfied. The final humiliation I had to endure was having a plug inserted into my anus and locked in place when my chastity belt was reattached for the night. I was then sent to Ashley's room to sleep on the floor next to her bed.